Phthalide

Phthalide
Phthalide Powder
Names
Preferred IUPAC name
2-Benzofuran-1(3H)-one
Other names
Phthalolactone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.586
UNII
  • InChI=1S/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2
    Key: WNZQDUSMALZDQF-UHFFFAOYSA-N
  • InChI=1/C8H6O2/c9-8-7-4-2-1-3-6(7)5-10-8/h1-4H,5H2
    Key: WNZQDUSMALZDQF-UHFFFAOYAW
  • O=C1OCc2ccccc12
Properties
C8H6O2
Molar mass 134.134 g·mol−1
Melting point 75 to 77 °C (167 to 171 °F; 348 to 350 K)[1]
Boiling point 290 °C (554 °F; 563 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phthalide is an organic chemical compound with the molecular formula C8H6O2. It is a white solid and the simplest benzo lactone. It is prepared from hydroxymethylbenzoic acid.[3]

Phthalides

The phthalide core is found in a variety of more complex chemical compounds including dyes (such as phenolphthalein), fungicides (such as tetrachlorophthalide, often referred to simply as "phthalide"), and natural oils (such as butylphthalide).

Examples

5-bromophthalide [64169-34-2] is used in the synthesis of Roxadustat and Citalopram.

3-(4'-chlorophenyl)phthalide is a chemical that serves function in the synthesis of Setazindol[4] & Chlortalidone.[5]

Uses

Phthalide has known uses in the synthesis of hydralazine,[5][6] & Pipethiadene.[7][8]

Phthalide is used in the synthesis of dibenzosuberone.

References

  1. ^ Kumar, R. Arun; Maheswari, C. Uma; Ghantasala, Satheesh; Jyothi, C.; Reddy, K. Rajender (2011). "Synthesis of 3H-Quinazolin-4-ones and 4H-3,1-Benzoxazin-4-ones via Benzylic Oxidation and Oxidative Dehydrogenation using Potassium Iodide-tert-Butyl Hydroperoxide". Advanced Synthesis & Catalysis. 353 (2+3): 401–410. doi:10.1002/adsc.201000580.
  2. ^ Kus, Nermin Simsek (2008). "Some oxidation reactions with molecular oxygen in subcritical water". Asian Journal of Chemistry. 20 (2): 1226–1230.
  3. ^ J. H. Gardner; C. A. Naylor, Jr (1936). "Phthalide". Organic Syntheses. 16: 71. doi:10.15227/orgsyn.016.0071.
  4. ^ Elks, J., Ganellin, C. R., eds. (1990). Dictionary of drugs: chemical data, structures, and bibliographies (1st ed.). Chapman and Hall. ISBN 9780412273001.
  5. ^ a b Vardanyan, R. S., Hruby, V. J. (2006). Synthesis of essential drugs (1st ed.). Elsevier. ISBN 9780444521668.
  6. ^ Druey, J., Ringier, B. H. (January 1951). "Hydrazinderivate der Phtalazin‐ und Pyridazinreihe". Helvetica Chimica Acta. 34 (1): 195–210. doi:10.1002/hlca.19510340122.
  7. ^ Protiva, M. (1983). "Pipethiadene Tartrate". Drugs of the Future. 8 (4): 334. doi:10.1358/dof.1983.008.04.65210. ISSN 0377-8282.
  8. ^ Polívka, Z., Rajšner, M., Metyš, J., Holubek, J., Svátek, E., Ryska, M., Protiva, M. (1983). "Antiaminic agents derived from thieno[2,3-c]-2-benzothiepin: 4-(1-Methyl-4-piperidylidene)-4,9-dihydrothieno[2,3-c]-2-benzothiepin and some related compounds". Collection of Czechoslovak Chemical Communications. 48 (2): 623–641. doi:10.1135/cccc19830623.
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